2,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol → 2,6,10,15,19,23-Hexamethyltetracosane-10,15-diol

HRID 596565Notes

Reaction equation

HRID 596565 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH3:32])[CH2:8][CH2:9][CH2:10][C:11]([CH3:31])([OH:30])[C:12]#[C:13][C:14]#[C:15][C:16]([CH3:29])([OH:28])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH3:3]>[Ni].C(O)C>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH3:32])[CH2:8][CH2:9][CH2:10][C:11]([CH3:31])([OH:30])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:29])([OH:28])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:25])[CH3:26])[CH3:1]

Participants

4

Reactant 1

HCID 214273422,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol

Product 1

HCID 136432652,6,10,15,19,23-Hexamethyltetracosane-10,15-diol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

In a 100 ml autoclave were placed 10 g of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol, 20 ml of ethyl alcohol and 1 g of W-5 type Raney nickel and the mixture was hydrogenated at 100° C under a hydrogen pressure of 50 ~ 60 kg/cm2 for 18 hours to give 2,6,10,15,19,23-hexamethyltetracosane-10,15-diol. The catalyst was filtered off and 1 g of Ni-catalyst supported on diatomaceous earth and 1 g of activated alumina were added to the filtrate, and it was hydrogenated at 200° C under a hydrogen pressure of 100 kg/cm2 for three days to give 7.7 g of squalane.

Workup

  1. customwas hydrogenated at 100° C under a hydrogen
  2. customfor 18 hours

Sources & evidence

ORD record
ord-67e68062bf3848b39656051dc5eca11f
Source dataset
uspto-grants-1977_03
Patent number
US04011277

Reaction notes

Loading…